Related Experiment Video
Updated: Jun 17, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Enantioselective B-H Insertion of Branched α-Alkyl Carbenes
Cheng-Da Zhang1, Chu-Xi Xu1, Zhang-Wei Wang1
1Academy for Advanced Interdisciplinary Studies, Frontiers Science Center for New Organic Matter, State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, College of Outstanding Engineers, Nankai University, Tianjin 300071, China.
Abstract:
The intermolecular asymmetric carbene transfer reaction of branched α-alkyl Fischer carbenes remains inaccessible due to their high susceptibility to rearrangement side reactions. This study overcomes these limitations by achieving copper-catalyzed, highly enantioselective insertion reactions of branched α-alkyl carbenes into B-H bonds. A variety of important chiral pharmaceuticals starting from readily available ketones has been effectively achieved based on this reaction platform. The precise modulation of carbene electronic properties and transfer reaction kinetics enables sterically demanding and unstable branched α-alkyl carbenes to undergo intermolecular transfer reactions with excellent efficiency and selectivity. The realization of versatile transformations of structurally diverse branched α-alkyl carbenes substantially promotes the development of carbene chemistry from both experimental and theoretical perspectives.
More Related Videos
08:56Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
09:33Formation of Covalent DNA Adducts by Enzymatically Activated Carcinogens and Drugs In Vitro and Their Determination by 32P-postlabeling
Published on: March 20, 2018
Related Concept Videos
Nucleophilic Aromatic Substitution: Elimination–Addition
Regioselectivity of Electrophilic Additions-Peroxide Effect
Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene
Electrophilic Addition to Alkynes: Hydrohalogenation
Conjugate Addition to α,β-Unsaturated Carbonyl Compounds
Radical Reactivity: Nucleophilic Radicals